August 2025
MESSAGE FROM THE BOARD
Is Investing in Short-Term Rentals Still Worth It in Today’s Market?
WHO AM I TO TALK ABOUT THIS?
I'm Steve Bell, Vice President of CAREIA (Chicago Area Real Estate Investors Association). My journey into real estate began just over three years ago. At the time, I was simply looking to supplement my W2 income—but I quickly became consumed with the learning process. Within 10 months, I had devoured hours of podcasts, articles, books, blogs, online forums, and conversations with investors. That’s when I found CAREIA—a place that has not only accelerated my growth but also connected me with like-minded investors who value action along with quality analysis.
Though my portfolio is relatively modest, I’ve built and operated exclusively in the short-term rental space for the past 2½ years. I’ve learned a lot—some of it the hard way—and I want to share what’s real (not just what’s hyped) about STRs.
IS THE STR HYPE REAL—OR JUST NOISE?
Depending on who you listen to, STRs are either gold mines or landmines. Some investors warn they’re too risky—citing cities cracking down with regulations or outright bans. Others say the key is to invest in markets where STRs are deeply rooted and immune to disruption. Then there’s the crowd shouting about “easy money,” while newer operators quietly bow out due to poor performance.
The truth? There’s some merit to all these perspectives—but no one has the whole picture. Here’s what I know: STRs can outperform long-term rentals significantly, but only when done right. And yes, the landscape is shifting—regulations are evolving because STRs are spreading fast, even in towns that never anticipated them. That means doing your due diligence is more critical than ever.
WHAT DOES A “GOOD INVESTMENT” LOOK LIKE?
Seasoned investors often say a good deal is one that cash flows now and appreciates over time. I agree. But most STR investors aren’t looking for a little cash flow—they’re looking for meaningful monthly returns.
If your STR brings in $500–$1,000 per month in net cash flow and appreciates around 3% annually, that’s a strong investment by most standards. Can you earn more? Absolutely. Can you lose money? Also yes.
Your stage of life, investment goals, and risk tolerance all play a role in whether a STR is right for you. Personally, my properties perform above the average. But that didn’t happen by chance—it happened through careful planning, market research, and strategic execution.
WHERE SHOULD YOU BUY A SHORT-TERM RENTAL?
Here’s the first and most critical step: Call the city. Ask what their STR regulations are and whether they’re investor-friendly. If a city regulates STRs and supports them, it’s usually a sign that STRs are welcomed—and profitable—there.
Next, ask yourself: Why would anyone travel here? If there’s no clear reason, it’s probably not a good market. I look for at least three major draws—reasons people visit again and again. It could be natural attractions, seasonal activities, or cultural events. A single big draw (like a national park) might work, but more is almost always better.
WHAT MAKES A LOCATION STRONG?
Every investor has their own checklist, but here’s mine:
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Natural Features: Beaches, lakes, rivers, mountains, dunes, forests, waterfalls
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Outdoor Activities: Hiking, boating, skiing, fishing, golfing, snowmobiling, ORV trails
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Seasonality: Does the area attract visitors in winter/fall and summer?
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Attractions: National/state parks, historic towns, popular landmarks, casinos
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Proximity to cities: Look 30–60 minutes outside a major city where STRs are banned or restricted
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College towns: Alumni weekends, graduation, and sports events drive demand
If your market checks several of these boxes, your chances of year-round bookings increase significantly.
WHERE SHOULD YOU NOT BUY?
A place where travelers come only for weddings, funerals, or the occasional family holiday is not enough. If the only reason people visit is to see relatives or attend life events—and there’s no high season—it’s not a solid STR market.
Yes, all towns see some travel. But if those visits aren’t consistent, and the town lacks clear, recurring draws, you’re likely to struggle with occupancy and pricing power.
WHAT’S YOUR EXIT STRATEGY?
Let’s be honest—short-term rentals are risky. You’ll invest heavily up front—not just in the property but in renovations, furnishing, and amenities that make your listing stand out.
And if bookings don’t come? You need a Plan B. Can you pivot the property to a long-term rental? A mid-term rental? Workforce or travel nurse housing? If you can’t make the numbers work across multiple strategies, it may not be the right deal.
Always buy with the exit in mind.
MY PERSONAL EXPERIENCE
My first STR opportunity came during a family vacation. We were searching for a rental near a popular lake and dunes region—only to find everything booked a year in advance. That was my lightbulb moment.
I dug into the data and found:
The area had a proven history of welcoming tourists, and the hotels weren’t cutting it anymore. Since then, we’ve had guests come for everything from beaches, to hiking, to fishing, to weddings, snowmobiling, and golf weekends. Some have even made it their annual tradition.
Because we did the work up front, we’re now reaping the rewards. It didn’t happen by luck—it happened by paying attention to the signs.
WHERE TO FIND SUPPORT (IF YOU’RE STR-CURIOUS)
If you’re thinking about getting into STRs—or want to improve what you already own—CAREIA is a great place to start. We host a Short-Term Rental Subgroup every 3rd Monday of the month at Portillo’s in Batavia (Randall Rd) from 7–9 PM.
Whether you're brand new or a seasoned investor looking to sharpen your edge, we’d love to have you join the conversation.
Steven Bell
Chicago Area Real Estate Investors Association - Vice President
| Upcoming Events |
CAREIA
Board of Directors
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Cash Flow Game Night (Members Only Event)
Wednesday, August 6, 2025 @ 7:00 p.m.
McDonald's off Highland Avenue
1 Yorktown Shopping Center, Lombard
https://www.careia.org/event-6252579
CAREIA Monthly General Meeting
Monday, August 11, 2025 @ 7:00 p.m.
Networking starts at 6:45 p.m.
Hyatt of Lisle • 1400 Corporetum Drive, Lisle
Topic: TBD
Key Note Speaker: Leticia Zertuche - Roca Construction
https://www.careia.org/event-6219957
Short Term Rental Sub Group Meeting
Monday, August 18, 2025 @ 7 p.m.
Portillo's Hot Dogs, 531 N. Randall Rd., Batavia, IL 60510
Anyone who has an interest in investing in short or mid-term rentals are invited to attend our monthly STR sub group meeting. Each month we will have an open forum to discuss all things short term rentals.
https://www.careia.org/event-6252574
Real Estate Networking Night
Monday, August 25, 2025 @ 6:30 p.m.
Portillo's Hot Dogs, 235 E. North Avenue, Glendale Heights, IL 60139
A FREE Member & Non-member Event
https://www.careia.org/event-6252575
Cash Flow Game Night (Members Only Event)
Wednesday, September 3, 2025 @ 7:00 p.m.
McDonald's off Highland Avenue
1 Yorktown Shopping Center, Lombard
https://www.careia.org/event-6280253
CAREIA Monthly General Meeting
Monday, September 8, 2025 @ 7:00 p.m.
Networking starts at 6:45 p.m.
Hyatt of Lisle • 1400 Corporetum Drive, Lisle
Topic: : TBD
Key Note Speaker: TBD
https://www.careia.org/event-6219962
Short Term Rental Sub Group Meeting
Monday, September 15, 2025 @ 7 p.m.
Portillo's Hot Dogs, 531 N. Randall Rd., Batavia, IL 60510
Anyone who has an interest in investing in short or mid-term rentals are invited to attend our monthly STR sub group meeting. Each month we will have an open forum to discuss all things short term rentals.
https://www.careia.org/event-6280248
Real Estate Networking Night
Monday, September 22, 2025 @ 6:30 p.m.
Portillo's Hot Dogs, 235 E. North Avenue, Glendale Heights, IL 60139
A FREE Member & Non-member Event
https://www.careia.org/event-6280246
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President: Pete Gordon
Vice President: Steven Bell
Secretary: Rob Hayes
Treasurer: Vanessa Krynen
Librarian: Dwayne Denzinger
Programing: PK Kleinert
Vendor: Iva Norris
Newsletter: Belinda Moore
Publicity: Mary Ann Skweres
Membership: Danny Galvez
Tech Support: Keith Jablonowski
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Our mission
To support and
promote local real estate investors
though networking, education, support, leadership on
legislative issues,
and promoting professionalism
and standards of excellence in the
real estate
investing industry.
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WORDS OF WISDOM
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"Inaction breeds doubt and fear. Action breeds confidence and courage. If you want to conquer fear, do not sit home and think about it. Go out and get busy." - Dale Carnegie
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Library Book of the Month
How to Win Friends and Influence People
How to Win Friends and Influence People by Dale Carnegie is one of the first best-selling self-help books ever published. Written by Dale Carnegie and first published in 1936 as a teaching aid for the self-development courses he has giving at the local YMCA, it has sold more than 30 million copies since then.
If you've ever asked yourself "what was he thinking?" or "how can I get this person to see things my way?", this book answers both of those questions again and again, through hundreds of real-life examples.
As relevant as ever before, Dale Carnegie's principles endure, because people have the same wants, needs and fears as 80 years ago. People will tell you what they want if you will listen. Using the principles presented in his book you will learn how to deal smoothly with your family, your boss and coworkers, your friends and acquaintances and achieve those win-win outcomes that make success so much easier and enjoyable.
Learn the six ways to make people like you, the twelve ways to win people to your way of thinking, and the nine ways to change people without arousing resentment.
Be the person that people enjoy dealing with and achieve your personal and professional success in the complex and competitive modern age.
Did you Know?
We have: Books, CD's, and even Movies!
Have you ever wanted to read a book or listen to a course but didn't want
to spend the money knowing if it was what you really wanted?
Well, that's what our Library is here for. It's for you to read, listen or even watch some great things on real estate without having to dish out the bucks!
Sometimes you will find you may want to purchase the book or program after you borrow it. Great, but aren't you glad you didn't pay for all the ones that just weren't right for you?
To check out materials:
- Only members can borrow materials
- Review inventory here: https://www.careia.org/LibaryList
- Fill out CAREIA Library request form
- Receive materials at the next General Meeting
- Materials are due back in one month
- Note. If materials are not returned, member is responsible for paying cost of materials for replacement.
